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<h1><a href="https://archiveofourown.org/works/25419409">Try, Try Again</a> by <a class='authorlink' href='https://archiveofourown.org/users/angelsandsacrificers/pseuds/angelsandsacrificers'>angelsandsacrificers</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>3 plus 1, 3 times, Boys Kissing, Flowers, Getting asked out, M/M</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-07-21</td></tr>

<tr><td><b>Updated:</b></td><td>2020-07-21</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-05 04:55:23</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,150</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/25419409</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/angelsandsacrificers/pseuds/angelsandsacrificers</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>3 times Dean tried to ask Cas out + 1 time Cas figured it out.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester, Dean Winchester &amp; Sam Winchester</td></tr>

<tr><td><b>Comments:</b></td><td>8</td></tr>

<tr><td><b>Kudos:</b></td><td>59</td></tr>

</table>

<a name="section0001"><h2>Try, Try Again</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>I know this has most likely been done before, but I don't care.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>
  <span>Sam was on house arrest until further notice. Even Dean can admit 4 back-to-back hunts is draining (especially at this age, which neither of them will willingly acknowledge). Since Cas was back in town, Dean decided they needed some time for themselves. Dean loved Sam with his whole heart, but he had also spent his whole life with the guy. They had to take a break at some point. </span>
</p><p> </p><p>
  <span>It didn’t take much work, in all honesty. Sam was mostly swayed by Dean’s urging to “process his emotions,” or whatever emotional bullshit Sam would’ve come up with anyway. Cas had promptly presented him with a case, and how was he supposed to say no? </span>
</p><p> </p><p>
  <span>That’s how he ended up driving through Ohio, exhausted beyond all belief because </span>
  <em>
    <span>what monster were they even trying to take down,</span>
  </em>
  <span> with an angel in the passenger seat squinting at worn out cassettes. It was almost pitch black that night. The moon was hardly a sliver in the sky, and the only thing illuminating the road was the Impala’s headlights and the occasional car that passed them on the back road.</span>
</p><p> </p><p>
  <span>“I’ve never heard you mention Van Halen before. Why do you have a cassette if you never play it?” </span>
</p><p> </p><p>
  <span>Dean dragged a hand over his face. “Sam had a phase. Their self-titled isn’t that bad.”</span>
</p><p> </p><p>
  <span>“Runnin’ With the Devil,” Cas scoffed. “If only he knew.”</span>
</p><p> </p><p>
  <span>“Yeah,” Dean snorted. He tensed. “Hey Cas…”</span>
</p><p> </p><p>
  <span>The angel regarded him.</span>
</p><p> </p><p>
  <span>“Say we figure out who this son of a bitch is, and gank it, and get back to the bunker alive, um, do you want to have dinner?”</span>
</p><p> </p><p>
  <span>Silence rumbled through the Impala. Castiel squinted at him. Dean hoped Cas couldn’t see his face flush.</span>
</p><p> </p><p>
  <span>“Dean surely you’ve noticed by now that I don’t eat.”</span>
</p><p> </p><p>
  <span>Dean pressed his lips tight together and let his shoulders fall. “Yeah I know,” he mumbled.</span>
</p><p> </p><p>
  <span>Cas cocked his head inquisitively as Dean pulled into an empty parking lot and hopped into the backseat.</span>
</p><p> </p><p>
  <span>“Hold down the fort while I catch some shut eye, okay?”</span>
</p><p> </p><p>
  <span>“No one shall breach the Impala’s mighty walls,” Cas said, completely monotone.</span>
</p><p> </p><p>
  <span>Scoffing, Dean relaxed in the backseat. He smiled when he heard Cas pop in the cassette and play Van Halen on a ridiculously low volume. Just as he was nodding off, he almost missed the gruff “Runnin’ with the devil,” that was sung with the track.</span>
</p><p> </p><p>
  <span>~~</span>
</p><p> </p><p>
  <span>Dean pulled into the motel’s parking lot for the second time that day, but only just noticing the beautiful purple blossoms growing by the sign. He swung Baby’s door open, grabbed the food, and headed toward the flowers. He picked a few stems before making his way into the room.</span>
</p><p> </p><p>
  <span>He tossed the food bag at Sam, who was researching on the bed. He grunted his thanks.</span>
</p><p> </p><p>
  <span>Cas was sitting at the table by the window reading through one of the library books. Gently, Dean placed the flowers in front of the angel. Cas looked up at him curiously.</span>
</p><p> </p><p>
  <span>It occurred to Dean in this moment that he had no plan. Why had he just given Cas flowers? Even Sam, nose deep in research, had looked up at the awkwardness that had settled over the room. He had a questioning eyebrow raised at Dean.</span>
</p><p> </p><p>
  <span>“Dean?” He looked back at Cas.</span>
</p><p> </p><p>
  <span>“Um… I thought they were uh… pretty.”</span>
</p><p> </p><p>
  <span>“So you gave them to Cas?” Sam asked. Damn him.</span>
</p><p> </p><p>
  <span>“Shut up,” he retorted and gave a contented grunt when he rolled his eyes and returned his focus to his research. Cas was still looking at him.</span>
</p><p> </p><p>
  <span>“Actually Dean, you have a good eye.”</span>
</p><p> </p><p>
  <span>“What?”</span>
</p><p> </p><p>
  <span>“Rowena mentioned recently that she was having trouble finding good lilac. I’ll recommend the area to her.”</span>
</p><p> </p><p>
  <span>Dean cleared his throat. “Oh yeah Rowena- I um- yeah I remembered that. Good memory Cas.”</span>
</p><p> </p><p>
  <span>He scurried over to the other motel bed, content to watch Dr. Sexy until someone turned something up.</span>
</p><p> </p><p>
  <span>~~</span>
</p><p> </p><p>
  <span>Dean shook his head after zoning out for the seventh time, trying to focus. He had to get out or he was going to lose it. They had been researching for four days. He wanted to slam his head on the table. That’s all they did these days. Research. He didn’t know how Bobby stood it. </span>
</p><p> </p><p>
  <span>“Hey I heard they opened up a new hiking trail at the park.” He grimaced inwardly.</span>
</p><p> </p><p>
  <span>“Oh really,” Sam inquired, not looking up. </span>
</p><p> </p><p>
  <span>“Yeah I was gonna head over and take a break” He stood up and shook out his limbs. “Cas, you wanna come?”</span>
</p><p> </p><p>
  <span>“Actually, I think I’m onto something here. I’ll stay.”</span>
</p><p> </p><p>
  <span>Cas hadn’t even taken his eyes off the book he was reading.</span>
</p><p> </p><p>
  <span>Sam yawned and stretched his back. “I could stand to stretch my legs. We’ll catch you later Cas?”</span>
</p><p> </p><p>
  <span>“I’ll be here,” he pronounced. </span>
</p><p> </p><p>
  <span>Dean tried not to feel disheartened as he climbed into the Impala with his brother.</span>
</p><p> </p><p>
  <span>~~</span>
</p><p><br/>
<br/>
</p><p>
  <span>Dean was still shaking leaves out of his hair when he fell into bed that night. He frowned when there was a knock at his door. </span>
</p><p> </p><p>
  <span>“Come in?” he called out.</span>
</p><p> </p><p>
  <span>Cas shuffled in awkwardly. “I was advised to do this in person,” he stated.</span>
</p><p> </p><p>
  <span>Dean squinted. “Do what?”</span>
</p><p> </p><p>
  <span>Cas seemed to be looking everywhere other than Dean. “I apologize for not seeing it earlier. Admittedly, I’ve been caught up with the matter of Heaven failing and trying to help out on cases. In my final defense, I know very little of human mating rituals.”</span>
</p><p> </p><p>
  <span>“Human </span>
  <em>
    <span>what </span>
  </em>
  <span>rituals-” Dean choked out. He gave Cas an incredulous look and swore the angel was blushing. Could angels blush?</span>
</p><p> </p><p>
  <span>“That’s- that’s what you were offering right? With dinner and the flowers and the park idea?”</span>
</p><p> </p><p>
  <span>“</span>
  <em>
    <span>Dates, Cas</span>
  </em>
  <span>,” Dean wheezed. “They’re called </span>
  <em>
    <span>dates.</span>
  </em>
  <span>” </span>
</p><p> </p><p>
  <span>“Oh well, then I accept. Or offer one. Or many. Um- Sam wasn’t exactly clear with the instructions-”</span>
</p><p> </p><p>
  <span>“You talked to Sam?” Dean was exasperated. </span>
</p><p> </p><p>
  <span>“He also told me to ‘proclaim my affections,’” Cas said somehow with a straight face. He cleared his throat. “I’ve felt something for you for a while now Dean. It was one of the main reasons Heaven reprimanded me in the early days. Zachariah called it ‘glaringly obvious,’ but you seemed rather oblivious, if I might say.” He paused. “But Dean I also feel a strong bond of friendship with you, so if this doesn’t work or whatever- I’d rather not lose you because you’re very important to me.”</span>
</p><p> </p><p>
  <span>Dean thought he was going to implode. Cas tilted his head and squinted.</span>
</p><p> </p><p>
  <span>“Oh my g- Cas get over here,” Dean demanded. </span>
</p><p> </p><p>
  <span>Cas started forward, and Dean grabbed the lapels of his stupid tan trench coat and slammed their lips together. It did hurt, and it was really a lot of teeth, but it was Cas. He put their foreheads together and gave Cas a watery smile.</span>
</p><p> </p><p>
  <span>“Yeah,” he said, voice thick. “Let’s go out or whatever. You mean the world to me Cas.”</span>
</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>Thank you for reading, and as always constructive criticism is super appreciated!</p></blockquote></div></div>
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